Showing Compound (+)-3-Thujone (FDB014960)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:34 UTC

Update date

2019-11-26 03:11:02 UTC

Primary ID

FDB014960

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(+)-3-Thujone

Description

(+)-3-Thujone, also known as beta-thujone or β-thujone, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (+)-3-thujone is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on (+)-3-Thujone.

CAS Number

471-15-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(+)-Isothujone	ChEBI
(1S,4S,5R)-(+)-3-Thujanone	ChEBI
(1S,4S,5R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one	ChEBI
[1S-(1alpha,4beta,5alpha)]-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one	ChEBI
beta-Thujone	ChEBI
D-beta-Thujone	ChEBI
D-Isothujone	ChEBI
trans-Thujone	ChEBI
[1S-(1a,4b,5a)]-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one	Generator
[1S-(1Α,4β,5α)]-4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one	Generator
b-Thujone	Generator
Β-thujone	Generator
D-b-Thujone	Generator
D-Β-thujone	Generator
(+)-b-Thujone	HMDB, Generator
(+)-beta-Thujone	HMDB
(+)-cis-Thujone	HMDB
(+)-Thujone	HMDB
-Thujone	HMDB
D-beta	HMDB
Isothujone	HMDB
(+)-3-Thujone	ChEBI
(+)-Β-thujone	Generator
alpha-Thujone	MeSH
cis-Thujone	MeSH
Thujone	MeSH
(-)-Thujone	MeSH
3-Isothujone	MeSH
3-Thujanone	MeSH
beta-Thujone, 1S-(1alpha,4beta,5alpha)-isomer	MeSH
alpha, beta-Thujone	MeSH
beta-Thujone, (1S-(1alpha,4alpha,5alpha))-isomer	MeSH
beta-Thujone, (1alpha,4alpha,5alpha)-isomer	MeSH
(+)-β-Thujone	biospider
[1S-(1α,4β,5α)]-4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one	Generator
β-Thujone	biospider
3-Thujanone, (1S,4S,5R)-(+)-	biospider
D-β-Thujone	biospider
D-β-thujone	Generator
Thujone, (+)-	biospider
β-thujone	Generator

Predicted Properties

Property	Value	Source
Water Solubility	0.44 g/L	ALOGPS
logP	1.74	ALOGPS
logP	2.28	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	44.54 m³·mol⁻¹	ChemAxon
Polarizability	18.02 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H16O

IUPAC name

(1S,4S,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one

InChI Identifier

InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8+,10-/m0/s1

InChI Key

USMNOWBWPHYOEA-XKSSXDPKSA-N

Isomeric SMILES

CC(C)[C@@]12C[C@@H]1[C@H](C)C(=O)C2

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

Classification

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Thujane monoterpenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

beta-thujone (CHEBI:50045 )
Bicyclic monoterpenoids (LMPR0102120039 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 78.90%; H 10.59%; O 10.51%	DFC
Melting Point	Not Available
Boiling Point	Bp 201-202°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D +72.46 (neat)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(+)-3-Thujone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00ou-9300000000-5ac67463cc6dff4e26c5	Spectrum
Predicted GC-MS	(+)-3-Thujone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-e5a1ab6ee8fcd2e7222d	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-7900000000-e4ab468ffb3afaf16129	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pe9-9000000000-960a6c7d4901afec9233	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-07a82b9f8d15764ed904	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-65761ceb0d88aa809b6a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9500000000-4023ebf09d9995d37111	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-e8b89c21a7958e185278	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pdl-7900000000-5c5ad8968d995b2431ac	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-8900000000-a32be7e7fd99fd0b8b23	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-9300000000-eac02498908e1d67934a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9400000000-22a79a891aa2c60d074e	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36113

CRC / DFC (Dictionary of Food Compounds) ID

JXM68-F:JXM64-B

EAFUS ID

Not Available

Dr. Duke ID

BETA-THUJONE|3-ISOTHUJONE

BIGG ID

Not Available

KNApSAcK ID

C00000836

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Thujone

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
abortifacient	50691	A chemical substance that interrupts pregnancy after implantation.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti feedant			DUKE
emmenagogue			DUKE
insectifuge	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE